It Was Always You
by GGNYC
Summary: Nate Archibald has fallen for a new freshmen. This story takes you through their friendship and their love and and drama. This is a N/J and C/B and possibly D/S story. My first fanfic please R&R disclaimer: I don't own anything
1. Prologue:Mysterious Girl

**A/N: this is my first fan fiction, I know it's a little slow at first but I promise it will get good so please review and let me know what you think! **

It Was Always You

Prologue: Mysterious Girl

"Who i_s_ that?" Nate Archibald whispered to his best friend Chuck Bass as they were engaging in one of Chuck's favorite sports. Freshmen hunting. Up until now, Nate had no idea why he came along. He already had a girlfriend, and was desperately in love with her best friend. So for him, there was really no point to this whole thing—that was, until he saw _her._ "Chuck," he protested, "who is that?"

"Which one?" Chuck asked annoyed that Nate was distracting him from deciding on his next prey.

"Her," Nate said pointing to a petite girl with long blond hair that fell just below her shoulders, and beautiful blue eyes who walked along the path to Constance Billard all by herself.

"How am I supposed to know Nathaniel?" Chuck asked, a cool tone in his voice.

"Please, like this isn't a game for you and you don't know the players," Nate laughed at his best friend.

"Since you are my best friend, Nathaniel, I'll run some stats and get back to you. After all, I can find out anything. I am Chuck Bass."

"Okay," Nate whispered, images of the beautiful mysterious girl swimming in his head.

"Nathaniel, not that I am against this in any way, but you do realize that you have a girlfriend and you also have a habit of falling for girls that are slightly unattainable, even for you."

Chuck's cold reminder made Nate think about Blair Waldorf, who had been his best friend for a very long time, and, I who, as everyone liked to say, he had been dating since kindergarten, and it made him think even harder about Serena Van der Woodsen, his other best friend, who he had been in love with all his life, and about whom he was keeping a terrible secret. "Yeah I know Chuck," he answered. "But I need you to do this for me. I need you to find out who she is so I can put all of this stuff to rest." With that he walked the opposite way that the girl had walked moments earlier, towards St. Jude's.


	2. Chapter 1: I've Got the Stats

Chapter One: I Got the Stats

"Nathaniel! I got those stats you wanted, and let me tell you, you're getting yourself into a fucking mess." Chuck Bass called down the hallways of St. Jude's raising an eyebrow at his best friend.

"Just give me that," Nate snapped back, grabbing the manila folder out of Chuck's hands.

"Alright, alright, just don't say I didn't warn you. And if you want any chance of ever speaking to this girl, you better make damn sure Blair never finds out what you are doing."

Nate was taken aback. What did Blair have to do with any of this? What did she have to do with this mystery girl? Blair was the last person that Nate Archibald wanted to think about right now--with the new mystery girl and the sudden return of his unrequited love, Serena Van der Woodsen. "Yeah, yeah, I'll be careful," Nate said when he finally snapped out of his daze. "But I'm just curious Chuck, what does Blair have to do with this girl?"

"Other then the fact that you're dating her and she is supposed to be the love of your life, and you already have feelings for one other girl, you should remember that your pretty little girlfriend is the Queen B at Constance. Any girl who wants to have any type of social life tries to get in with the girls of the steps, which means trying to become friends with Blair Waldorf. This girl is one of their prime candidates, which means your girlfriend and the bitches that follow her around will be watching her every move, and are already making her life a living hell. I'm just saying, you better watch yourself Archibald. Unless you want to find yourself in the middle of a Gossip Girl worthy love triangle—oh no wait, I guess in your case it'd be a square," Chuck laughed and smirked a bit his own joke.

"Thanks for the lecture, Chuck, like you're really the pillar of morality that I want to be taking advice about women from. Have you ever even had a steady girlfriend?" Nate

snapped back angrily.

"Why choose one? Life is so much more fun when you can have them all Nathaniel," Chuck answered Nate's question with his usual cockiness.

Nate rolled his eyes at his friend's response, wishing for just a moment that he could be as immoral as Chuck. But he knew that he had to do something. For now he was just going to have to keep everyone in the dark. He had to find some way to meet this girl, but first he had to find out who she was. Nate walked out to the courtyard and cautiously opened the folder.

**A/N: I promise that you'll find out the identity of Nate's mystery girl in the next chapter.**


	3. Chapter 2: The Steps of the Met

Chapter 2: The steps of the Met

Nate Archibald stood alone in the St. Jude's courtyard and took a few deep

breaths before looking at the contents of the folder he had opened just a few seconds earlier. Something inside of him felt like this wasn't right. He felt like gathering information on girl this way was something only Chuck Bass. Still, he had to know, if only put his mind at rest and move on with his life. So, Nate took a page out of the Bass playbook and looked down to the open folder in his hands. Right before his eyes, were Facebook pages, photographs, and even more information on his mystery girl.

"Jenny Humphrey," Nate said out loud reading her name off the top of the paper in the folder.

Why did that name sound so familiar to him?? He was sure he had never met her before in his life. He thought about it for a few minutes, but his concentration was broken by the ringing of the bell that meant lunch had begun. Nate decided that he would forget all about Jenny, and go see his girlfriend Blair Waldorf, before meeting up with Chuck in Central Park to smoke some weed.

He walked down Museum Row and headed towards the steps of the Met, where Blair and her friends always sat. Just as Nate was about to reach the steps, he saw her. She was rushing to the steps too, looking scared to death that she wouldn't make it.

"Jenny Humphrey," a girlish voice that Nate recognized as that of his girlfriend called out to the little freshmen as she ascended the steps.

"Jenny", Blair repeated, "you've kept me waiting and I don't like it when people keep you waiting."

"Yeah I know Blair," Jenny said apologetically, it's just that my brother wanted—

"Enough," Blair cut Jenny off before she could finish her thought; "I really don't care about your brother or anything else in your life for that matter. If you want to be one of us you need to obey my rules."

Nate couldn't watch his girlfriend rip apart Jenny Humphrey anymore, he stepped forward in her line of sight.

"Blair, Nate called cheerfully."

"Sweetie," Blair was shocked and excited to see her boyfriend, things had been a little tense between them ever since Serena Van der Woodsen had come back to town. But right now, with him standing there in front of her all of that seemed to be forgotten.

"What are you doing here?" Blair finished her thought.

"Well, I just thought I would stop by and see you, you are my girlfriend after all," Nate laughed at the absurdity of Blair's question as he kissed her on the cheek. "Oh, and I couldn't help but overhear your conversation as I was walking up," Nate said, it's my fault that Jenny is running late, you see her brother and I are friends and he always talks about her so I told him I wanted a chance to meet her and that's why she is late. I'm sorry if I got you into any trouble Jenny."

"Ththat's alright," Jenny stammered trying to figure out why this incredibly hot guy who she had never met was making excuses for her and sticking up for her in front of his girlfriend.

"Wait a minute," Blair said suspiciously, Nate, you're friends with Dan Humphrey. Why?

_Of course! That's how he knew her name! Dan Humphrey the uncool kid from Brooklyn who was in their grade, she was his little sister._ Nate quickly cleared his head and thought of an answer to Blair's question.

"Dan is an alternate on the soccer team, and he's been playing a lot more because half the team is out with mono, and since I am the captain I know everyone team, even Dan Humphrey, Nate said without missing a beat.

"Oh," Blair said, a little shocked. "Well then, Little J I guess I can give you a break this time, but you better have those invitations to the Kiss on the Lips Party done by tomorrow like you said you would. Tell you what, I'm in a generous mood make yourself one and make one for a friend."

"Okay!" Jenny was shocked at the turn of events, just moments ago she'd been sure she would be banished from the steps for good and now she was being invited to the Kiss on the Lips party by Blair Waldorf herself.

"Well, I don't want to keep Chuck waiting too long, you know how he can be", Nate said skillfully excusing himself from the Steps.

"See you later, honey," Blair said as Nate headed down the steps and towards Central Park.

Jenny waited until Blair was busy insulting the fashion choices of some other freshmen girl who hoped to join the girls of the steps, before making her escape. Jenny snuck down the steps and headed after Blair's boyfriend.

"Hey! Wait up," she yelled after him when she was sure he was in earshot.

"Yeah?" Nate replied as he turned towards her.

"Why did you do that?" Jenny asked.

"Do what?" Nate played dumb and flashed one of his brilliant smiles in Jenny's direction.

"Tell Blair that it was your fault I was late. I don't know you and I'm almost 100% sure you don't know my brother and I know Dan doesn't play soccer, even though he's really good at it. So what's the deal?" Jenny was intrigued as she waited for him to answer the question.

"I don't like it when Blair picks on people, and you seemed like a nice girl so I figured I'd help you out," he answered her naturally.

"Well thanks very much, but for future reference I can handle myself and I definitely don't need some knight in shining armor to come rescue me," Jenny quipped back.

"Fair enough," Nate said, "but just because you don't need a knight in shining armor, doesn't mean you could use a friend. We haven't been formally introduced, I'm Nate Archibald."

"I'm Jenny Humphrey."

"Well, Jenny Humphrey, it was nice meeting you why don't I give you my number-- just in case you ever decide you're in need of my help or just my friendship," Nate Archibald said with a flirting smile that Jenny was too naïve to pick up.

"Well, okay I guess," said Jenny as she held out her phone, excited to have somebody who actually wanted to be her friend.

"Now don't lose that number," Nate said with a laugh as he handed her back her cell phone.

"I won't," Jenny promised him as she turned to walk away.

"Jenny, I need you to promise me something else," Nate called after her.

"Yeah? And what is that Nate Archibald?" Jenny asked him jokingly.

"I need you to promise me that you won't tell anyone, not your brother, not Blair, not anyone at all what we talked about okay. Oh and Jenny, promise me you won't be too afraid to ask me if you ever need help, really I mean it.

"Yeah, Nate I promise no one will find out about our little conversation, after all I really don't want Blair to be mad because I talked to her boyfriend. I mean how stupid would that be? It's not like you actually like me or anything! So it's no big deal," Jenny replied to Nate's request honestly and walked off in the other direction back to the steps of the Met.

Nate smiled after Jenny as she walked away from him. Maybe he didn't need another girl to be in love with. Maybe all he wanted was someone to talk to who wouldn't judge him or expect to be anything he wasn't. Yes, Jenny could be his friend and she could talk to her and maybe even take care of her if she would let him. Yes, he's thought being her friend would be just fine and would have to do for now, because right now Nate Archibald had a bigger problem on his hands... Serena Van der Woodsen.

**A/N: in the next chapter, we're going to take a break from Nate's point of view and look at Jenny's life a little bit, plus we're probably going to hear a little bit about how Chuck is feeling about what Nate is doing to Blair. **


	4. Chapter 3: Central Park

**A/N: I know you were expecting Jenny's point of view, but I decided to change the order of the chapters around a little bit. Here is some Chuck for you.**

Chapter three: Central Park

**Spotted: Nate Archibald looking forlorn with Chuck Bass in Central Park. What's the matter N, C not quite the company you were looking for?**

"It sure took you long enough," Chuck said to Nate, tossing him a joint, "In the mood for some herbal, Nathaniel?" Chuck asked with a sly smile. "So what happened to you? Blair Waldorf steps a little too much for you to handle?

"No, no Chuck nothing like that," Nate said while blowing little circles of smoke from his mouth out in front of him, "it's just that I saw_ her_ again."

"Who?" Chuck asked the slightest hint of annoyance in his voice. Nate had the most amazing girlfriend and yet he was never satisfied. He either wanted Serena was some other mystery girl, but never Blair, Chuck just didn't understand it. He was the self-proclaimed womanizer, and even he thought he was being greedy.

"Jenny!" Nate said a little too loudly.

"Oh you're still not over her," Chuck said his voice full of sarcasm. He really didn't like to hear Nate talk about this girl, but Nate was his best friend, so he tolerated it. Still, Chuck didn't understand why he felt so upset when he thought about what Nate was doing to Blair. It wasn't he had feelings for her anything, was it? "What's the matter Nate? Is Blair no good?" Chuck asked with a laugh.

"What do you mean?" Nate asked.

"You know exactly what I mean," Chuck answered.

"Oh that," Nate said with a laugh, "I really don't know, I mean we haven't."

"Nathaniel, you need to seal the deal," Chuck said.

"Seal the deal? Who says seal the deal?" Nate laughed. "I don't know Chuck; don't you ever feel like our whole lives have been planned out for us? Don't you think we're entitled to have some choice in the matter?

"What we're entitled to, Nathaniel is a trust fund, a house in the Hamptons, and maybe a prescription drug problem and you are entitled to tap that ass," Chuck said with a smile, the last statement referencing Nate's inability to sleep with Blair.

"Chuck," Nate said, "what should I do about Serena?"

"Forget about her," Chuck answered simply, "she is nothing, she is a slut, she's not worth it.

Nate frowned he couldn't help feeling that Chuck was right and wrong at the same time. But he knew he couldn't just forget about Serena. He had to tell Blair his secret, even if it meant she might hate him forever.


	5. Chapter 4: Emergency 911

**A/N: Thanks so much for all the reviews!!! Jenny chapter as promised!!! Italics=thoughts. Kiss on the Lips will be in next few chapters. **

Chapter four-Emergency 911

**Jenny (mobile)**

**Help!! **

**Emergency! **

**I need you!**

**712 5****th**** Ave**

**J.**

Dan Humphrey looked down at the text message on his cell phone._ Why did Jenny always need him? Why did he always feel so compelled to be a good big brother and run to her rescue no matter what? _ Something inside Dan knew this was a trap. He knew he should just text his little sister back and tell her he wasn't coming, tell her he was going to fall for her tricks this time. However, Dan also knew that telling Jenny "no" would do no good. If there was one thing that Dan Humphrey knew for sure it was that his little sister Jenny was relentless. Jenny would do anything to get what she wanted or needed, and right now she needed his help. Dan boarded the subway, too clueless to know what he was getting himself into.

As Dan exited the train and headed to 712 5th Ave. he got another text from Jenny:

**Jenny (mobile)**

**Dan!! Where RU? I really need you!!**

**When you get here I'm upstairs!**

_She'll never change, and neither will you. You always drop whatever you're doing help her it's just what you do. And now with mom gone, you really have to take care of her, it's your job. You're her big brother._ Dan thought to himself and reluctantly headed into 712 5th Ave. better-known as Bendel's department store._ What am I getting myself into?_ Dan wondered helplessly as he took the elevator up to the dress department where his little sister was waiting.

"You said you had an emergency?" Dan asked Jenny sarcastically when he saw her standing in front of a full-length mirror in a knee length red dress.

"Yeah", Jenny replied, "a fashion emergency. How do you think this looks?" Jenny asked her big brother

"Uh", Dan replied, "I think you look nice." Dan tried his best to help Jenny, but you really didn't know much about fashion. However, with their mom staying in Hudson, and their dad being, as Jenny put it, "allergic to department stores" Dan was his little sister's last hope.

"Yeah," Jenny replied in a whisper talking half to herself and half to her brother, "it's just too bad it costs more than a month's rent in the loft, but I'm pretty sure I could make something that looks like it."

"You look so pretty," said a voice from behind Dan and Jenny. Jenny turned around to see Serena Van der Woodsen standing behind her and her brother missing in action. Dan had a crush on Serena ever since she said hi to him at a birthday party in ninth grade. That had been the last party Dan had gone to.

"Thanks!" Said Jenny enthusiastically, "I'm Jenny Humphrey."

"I'm Serena Van der Woodsen."

"I know—I mean nice to meet you," Jenny answered star struck.

"What's it for?" Serena asked Jenny.

"The Kiss on the Lips party," Jenny answered proudly, "I'm making the invitations, so Blair said I could go! Strangely, your name wasn't on the guest list, but I can make you an invitation if you want one, after all Blair said I could make one for a friend. Just don't tell her you got it from me."

"Thanks but no thanks, Jenny," said Serena as she walked away, it was nice meeting you." "Oh, and Jenny that dress would look even better in black."

"Thanks for the advice Serena," Jenny called after her. This day turned out to be one of the best days in Jenny Humphrey's life. She got invited to one of the biggest social event of the year, she hadn't been banished from the steps, she spoke to Nate Archibald, and she'd met Serena Van der Woodsen. Jenny smiled happily as she went to look for her brother Dan.

"Dan!" She laughed as Dan came out from his hiding place behind the display, "I had no idea you could move that fast!"

"Yeah, well your fashion emergency was over so I figured…" Dan tried to hide his true reason for leaving.

"You know Dan, she's pretty nice, I bet you would find out you actually talked to her," Jenny said with the meddling voice of a little sister.

"Sure Jen, except that girls like Serena never even look at guys like me, let alone talk to them," Dan answered his sister in a melancholy tone of voice.

"But Dan I really think you would be surprised if he just gave her a chance, I mean what have you got to lose, it's not like you have any social life anyway," Jenny whined and protested expertly at her older brother.

"JENNY, I WOULDN'T EVEN KNOW WHAT TO SAY TO SOMEONE LIKE HER, SO PLEASE JUST DROP IT," Dan yelled angrily, sick of Jenny's nagging and desperately wanting to leave the stupid store. "I'm out of here, Jen"" Dan said and headed downstairs. As he stepped out of the elevator he noticed his sister had followed down using the escalator. Dan also saw a cell phone lying on the ground in front of him he picked it up and opened it. He saw Serena's picture on the inside._ This is her phone, she's probably looking for it, and I should get it back to her._

"She's staying at the Palace Hotel, you should go return that to her," Jenny said almost as if she had read Dan's thoughts.

"Yeah, maybe I should," Dan said he couldn't help feeling as if the fate had intervened for him.


	6. Chap 5:Things Come Together & Fall Apart

Chapter Five: Some Things Come Together and Others Fall Apart

**Spotted: Lonely Boy smiling outside of the Palace Hotel, maybe not so lonely anymore. **

_I can't believe it, I can't believe it!! I just went there to return her phone, and now I'm actually going on a date with Serena Van der Woodsen. I didn't even ask her out, she asked me. Okay, so maybe she was just trying to avoid going to the stupid party that Jenny has been obsessed with for weeks, but still, she chose me over all her rich friends, she chose me. I'm actually going on a date with Serena Van der Woodsen. Maybe I should listen to Jenny's advice more often. Maybe she actually knows what she's talking about._ Dan Humphrey shook the last two thoughts from his head, he definitely should not listen to his sister's advice more often, and she definitely did not know what she was talking about. After all, she desperately wanted to be accepted by Blair Waldorf, the Queen Bitch at Constance. But he definitely was going on a date, or something like that, With Serena Van der Woodsen, the girl he had been in love with since ninth grade. He thought back on the events that led to this momentous occasion:

_He had gone in to the Palace Hotel with the simple intention of returning Serena Van der Woodsen's cell phone that he found in Bendel's that afternoon, while he was helping his little sister Jenny with her "fashion emergency". He was leaving the phone at the front desk, when Serena had come downstairs. The man at the desk called her over and told her that Dan had found her phone, and returned it. Dan had just wanted to run away and hide, because he was seriously afraid that Serena would think he was a freak or a loser. Instead, she came over to him and thanked him profusely for returning her phone and asked him where he found it. Dan was embarrassed ,but he admitted that he found her phone while helping his little sister find it just for some party called The Kiss on the Lips party, but quickly added that he had been forced to store under the false pretenses of an emergency. "Oh it's okay, I drag my little brother to the store with me all the time," she told him. "I think I may have seen your sister there, her name is Jenny, right?"_

_"Y--Yeah," Dan had responded absolutely shocked that he was having a conversation with Serena about Jenny of all things._

_"She was really sweet, but if you are there with her, where were you?" Dan remembered the question Serena asked him her sweet voice echoing in his head._

_"I—I ran to the bathroom," he answered unable to think of a better excuse. Then it happened Serena's mom came downstairs, and started telling Serena something about the party. Dan remembered the way Serena's face and looked at the mention of the party, he can clearly tell she did not want to go. Her mom kept pressing the issue though, and Serena had searched for an excuse for not going to the party. That's when she turned and smiled at him._

_"I—I can't, I already made plans," Serena told her mother._

_Dan remembered the scornful look on Serena's mom's face when she asked her, "Oh? With who?"_

_Serena replied effortlessly, "With him," she had said pointing at Dan._

_Dan remembered that he had stood there. shocked, for just a millisecond, before replying, "yeah, that's right Serena and I have plans,"_

_Serena's mom had looked slightly suspicious and shocked, but instead of pushing the matter she simply asked Dan, "what's your name, and what are your plans with my daughter this Friday?_

_"I'm Dan Humphrey, and I am taking your daughter to a Lincoln Hawk concert, they were named one of the top forgotten bands of the 90s," Dan remembered replying without missing a beat._

_At that, Serena's mom had headed back upstairs, leaving Dan and Serena alone. He had been sure she was going to thank him for his help, and then ask them to leave, but instead, she asked him, "so you'll pick me up on Friday then?"_

_He had been shocked, "What?" He had replied _

_"You'll pick me up on Friday, you know, for the concert?" She had laughed beautifully at him._

_"But you barely even know me; do you really want to go out with me?" Dan had asked her incredulously._

_"Well, I figure I can give you a shot, you can't be worse than the people I do know. So is eight o'clock good then?" She had replied._

_"Yeah, eight o'clock is just fine," he answered on his way out._

This scene had been replaying in Dan Humphrey's head outside of the Palace Hotel, when he was brought back to reality by the wail of sirens on New York streets. At that point, Dan Humphrey decided it was time to go home and thank Jenny for making him go to the hotel in the first place.

**Spotted: N and B in a heated argument outside of B's apartment building. Do I detect some trouble in the kingdom?**

"I CAN'T BELIEVE YOU, I CAN'T BELIEVE YOU, I CAN'T BELIEVE YOU WOULD DO THAT TO ME!!" Blair Waldorf screamed at the top of her lungs. "I CAN'T BELIEVE I WAS ACTUALLY GOING TO SLEEP WITH YOU, AND YOU WERE HIDING THIS FROM ME ALL THAT TIME! AND WITH HER, OF ALL PEOPLE, YOU SLEPT WITH MY BEST FRIEND?" The tears now run down Blair's cheeks as she looked up at Nate Archibald, "H—HOW COULD YOU!! HOW COULD SERENA!! WHY WOULD YOU GUYS DO THIS TO ME???"

"Blair," Nate said rather calmly, "it happened one time, and then she was gone. I just didn't see the need to tell you, but I can lie to you anymore, I just can't!" He knew he had to convince her not to break up with him. When the fight started he realized he hadn't thought through the process, their parents were in business together and his dad would never forgive him if a breakup with Blair compromised the business relationship. "I promise this will make things better I won't ever see her again. I won't talk to her, I won't look at her, it'll be like she doesn't even exist. It's in the past Blair I promise!"

Blair liked it when Nate begged and she had been with him for so long, that at that moment she couldn't imagine life without him. Plus, she liked the idea of her traitor best friend Serena suffering as a social outcast. So she decided to forgive him, after all she couldn't go dateless to Kiss on the Lips. "You promise that it's in the past, you promise you won't speak to her at all?" Blair questioned her boyfriend.

"I promise Blair. It's over. It's done with. You're the only person I have feelings for; Nate Archibald lied with amazing ease. He wondered why he had chickened out. He wondered why he couldn't just tell Blair he needs to move on._ Maybe I really do love her, maybe Blair is the one for me._ Nate convinced himself that he was meant to be with Blair and that none of the other girls he thought about meant anything to him._ Not Serena, not,_ he paused as he thought her name, _Jenny. He didn't want anyone else but Blair,_ he assured himself. He gave Blair a kiss on the cheek and told her he would come in the limousine at 8:30 on Friday night to pick her up for the party. Then Nate left, and called Chuck Bass to tell him what a stupid thing he had just done.

**A/N: I know this chapter is a little long and boring, but it's important it sets the stage for everything that's going to happen at the party. To be clear this story does not end at the party it only just begins. The Gossip Girl blasts are used in this chapter to change the scene. The first part is all in italics because Dan is thinking about it. Thanks so much for all the reviews and support. Please tell me what you think of this chapter!**


	7. Chapter 6:Kiss on the Lips

**A/N: Sorry it took so long. I hope you like it! There are some lemons in this chapter. Please let me know what you think! Thanks for the reviews and support! **

Chapter Six: Kiss on the Lips

Chuck Bass looked down at his cell phone and picked it up.

"Yes Nathaniel, what's the problem?"

"I made a huge mistake Chuck; I don't know what I was thinking."

After Nate said this Chuck automatically assumed that Nate was referring to breaking up with Blair Waldorf. Chuck knew he had been planning on doing it ever since Serena Van der Woodsen had got back to town, and ever since he laid eyes on that stupid little freshman girl, Jenny Humphrey. _Sure she was pretty, it wasn't like he would ever turn her down, however he would take one Blair Waldorf over 1 million Jenny Humphreys any day._

"Chuck," Nate's voice called over the other end of the phone, "I made a huge mistake, I'm so stupid, I didn't break up with Blair, I—"

Chuck didn't hear the rest of Nate's statement; he was in too much shock._ Nate thought it was a mistake not breaking up with Blair. Blair was so pretty, so pure, so powerful—what the fuck did Nate Archibald see in that dumb little freshmen Jenny Humphrey? She was nothing next to Blair. She was a dumb and pathetic wannabe from Brooklyn. She didn't have the class or the beauty of an Upper East Side princess, like Blair Waldorf, Jenny Humphrey was a pathetic imitation at best, and his best friend wanted her so badly. And as far as Serena Van der Woodsen was concerned, she was nothing more than a slut. Good for a fuck but nothing else. Serena was no better than the women Chuck paid for. There was no mystery to her. No beauty. No purity. No perfection. She was not even close to Blair. What the fuck was he thinking?_

"Chuck? Chuck? Are you there?" Nate's voice brought Chuck back to reality.

"Yeah Nathaniel I'm here," Chuck answered trying not to let on how disgusted he was, after all he was a self-proclaimed womanizer, so who was he to judge.

"Well then, what should I do?"

_Be happy with the girl you've got! Treat her right! Forget about Serena! Forget about stupid Jenny Humphrey from Brooklyn!_ Chuck wanted to scream these thoughts into the phone at Nate. He wanted to make Nate understand how lucky he was. He wanted to shake his best friend and scream "WHAT THE FUCK IS WRONG WITH YOU? WHAT THE FUCK ARE YOU THINKING?" But he didn't, he couldn't, because Nate Archibald was one of his only true friends, and somewhere buried deep down inside Chuck Bass was nothing more than a coward. So instead he said, "Relax, Nathaniel, get yourself together, get ready for the party, and please, for all of our sakes, seal the deal with Blair, this whole vow of celibacy thing you two have going on is making you too crazy for your own good, Nathaniel." Chuck cringed at his own advice, because in all honesty, the last thing he wanted Nate to do was sleep with Blair Waldorf. Chuck hung up the phone and sat for a minute, thinking, planning, and, of course, scheming. Soon he came up with an idea,_ if Nate has the girl I want, I'll take the girl he wants._ Chuck thought devilishly to himself. It would be easy; all these wannabe girls were always looking for an inner circle hookup. He was absolutely sure that little Jenny Humphrey would be no different. And he was Chuck Bass he could have any girl that he wanted, well almost any girl. A few minutes later, Nate and Blair arrived in the limousine to pick him up for the party._ Let the games begin,_ thought Chuck Bass with a smile,_ Oh yes let the games begin._

**Spotted: Little J exiting a cab at the entrance of her first Upper East Side Party. Careful J you're playing with the big boys now.**

Jenny felt out of place moment she walked in. Most people at the party were upperclassman and she barely knew anyone. She hoped Dan would come with her, after all she's made him an invitation, but he had somehow scored a date with Serena Van der Woodsen, and so Jenny was all on her own. She stood by the bar in her beautifully hand sewn black dress, and chatted with people as they passed. All of a sudden she noticed someone watching her from across the room. On the other side of the room, Chuck was watching Jenny and talking to Isabel Coates.

"Who's that?" Chuck asked if the, pointing to Jenny. He asked the question in a completely serious and interested tone, although he already knew the answer. He knew she was Nate's new obsession.

"That's Jenny Humphrey, she's a freshman," responded Isabel.

"Anything about her on Gossip Girl?" Chuck asked Isabel out of curiosity.

Isabel quickly looked down her Blackberry, checking Gossip Girl for any sign of Jenny Humphrey's name, any indication of her existence on the all too important website that revealed the secrets of Upper East Side teenagers in their world. "No," Isabel responded quickly, and then added with a smile, "at least not until you're done with her."

_Isabel has no idea how right she was. Chuck's plan was working perfectly. Jenny Humphrey was new and pure. All Chuck had to do was convince her to hook up with him and ruin her for Nate. He would show his best friend that his stupid freshman obsession with no better than any other girl in school. Chuck would prove to Nate for Jenny Humphrey wasn't special and that she wasn't worth his time. Chuck would show Nate that Jenny Humphrey could never compare to Blair Waldorf. If nothing else, Chuck would make Nate feel the sense of loss and pain that Chuck felt every time he saw Nate and Blair together. He would take something that Nate desired and coveted in make it his. He would take Jenny Humphrey away from Nate._ "Oh how I love freshmen," Chuck laughed at Isabel as he got up and headed to the bar, where Jenny Humphrey was standing.

**Spotted: C. eyeing Little J. at the Kiss on the Lips Party. Just hope he can keep it PG-13.**

"Hi, I'm Chuck," Chuck said to Jenny taking her small manicured hand in his and holding it gently with his trademark scarf still around his neck.

"I know –I mean—hi I'm Jenny," Jenny laughed, feeling flattered and a little bit nervous that someone like Chuck Bass would spend his time having a conversation with somebody like her.

"It is nice to meet you," Chuck said while playing with Jenny's hand which he still held in his, and trying to ramp up his level of charm.

"It is nice to meet you too," Jenny answered with a nervous giggle that revealed her naivety.

"Thank you," Chuck said, looking into Jenny's blue eyes and giving one of his trademark Chuck Bass smirks. He played with her hand, massaging it just a little bit. Jenny laughed and smiled, turning her face away from as she blushed.

_You've got her under your spell. This will be super easy,_ Chuck told himself, feeling confident in his ability to get Jenny to hook up with him. After a few more minutes, Chuck took Jenny's hand that he had been holding and started to lead her away from the busy dance floor. "Let's go somewhere quieter and talk," he said, still moving away from the mass of people.

"Okay," Jenny agreed hesitantly, looking around the room for someone else to talk to, or some reason to excuse herself from the situation, but she found nothing. She realized she didn't have much choice but to go with Chuck, since he was holding on to her arm and moving her along, but she told herself not to worry. _He's being nice to you. He only wants to talk and get to know you better. He's friends with Blair, Nate and, Serena stop being so worried!! _As they passed the bar, Jenny grabbed her purse and Chuck grabbed a bottle of champagne. As Chuck led her up a staircase in search of some quiet, Jenny kept reassuring herself._ He just wants to talk! You're being a baby! Stop worrying! _

"It certainly is quieter up here, but do you actually know where we're going?" Jenny asked Chuck with an incredibly nervous laugh.

"Here looks just fine," Chuck said positioning himself in front of Jenny in an alcove and trying to kiss her.

"You said you wanted to talk? What do you want to talk about?" Jenny asked Chuck, turning her face away from his lips and hoping he would get the hint.

"How into you I am," Chuck responded, pulling Jenny's face towards him and kissing her. Jenny felt his tongue push against her lips and pulled back. _What did Chuck think he was doing? This was so uncomfortable._

"I'm sorry," Chuck said sensing her reluctance and pulling away, "If you don't want to do anything that's okay. Let's start over."_ What is this bitch's problem? Why is she being so difficult?  
_

"Great! Do you want to start over back at the party?" Jenny asked Chuck hopefully and went to head towards the staircase.

"Have a glass of champagne—please?" Chuck asked Jenny, grabbing her arm and keeping her there.

"Well, okay maybe just one glass," Jenny agreed with a smile. _Okay, this is your chance, while he is distracted you can text for some help. _Jenny discreetly pulled out her phone and pulled up Dan's number._ Dan might be far away, you need a back up plan. _But who? The only person Jenny could think of at the party was Blair and there was no way she would come._ But Nate's here, _Jenny suddenly remembered and thought of the conversation they'd had the first time they met:

"_I definitely don't need some knight in shining armor to come rescue me," she had told him. Then he made her promise him something._

"_Oh and Jenny, promise me you won't be too afraid to ask me if you ever need help, really I mean it." _She recalled his words and hoped he really had meant it as she pulled his number up and put it into the text along with Dan's.

**ITS JENNY PLEASE HELP!!**

Was all she could manage to type and send before Chuck turned back to her with a glass of champagne.

"Let's go up to the roof. The view of the city is so beautiful from up there, you really should see it," Chuck said kindly.

"Okay," Jenny agreed. Anything that would keep Chuck busy and off of her until help arrived was a good idea in her book, and he seemed really excited about it.

**Spotted: Little J. in trouble on the roof with C. Hopefully Little J. can find a knight in shining armor to come and rescue her.**

As soon as they got up to the roof, Jenny knew she'd made a big mistake. Chuck started kissing her again, but this time when she tried to pull away, he wouldn't let her go and he didn't stop. Instead, he pushed her down against a skylight and stuck his tongue down her throat, pulling at her dress. She tried desperately to fight back. She tried to push and kick him away, but it was no use. He pinned her arms against the skylight and pushed her body back so her legs were useless.

_Why am I so stupid? Why did I trust him? Why is he doing this to me? There are tons of willing girls downstairs, why does he want me? What should I do? Where is Dan? Where is Nate? Are they coming? _The thoughts raced through Jenny's head as Chuck continued to kiss and grope her.

"NO! STOP! GET OFF ME!!" Jenny screamed at all opportunities.

"Shut up, you stupid bitch," Chuck hissed back at her._ Nobody ever rejects me, I'M CHUCK BASS! We'll see how Nate likes you now, you stupid slut bitch! Why are you making this so difficult? You led me on!!_ Chuck thought as he pulled at Jenny's dress.

Meanwhile downstairs and across town Nate and Dan felt their cell phones vibrating.

**ITS JENNY PLEASE HELP!!**

They both read the frantic SOS and sprang into action. Nate knew Jenny was at the party so he bolted from the dance floor and started looking for her.

"Nate! Where are you going?" Blair yelled after him.

"I need to take a walk," Nate yelled back, without taking time to think of a good lie._ Jenny is in trouble, she needs you. You better find her fast!_

On the other side of the city, Dan was hailing a cab and explaining things to his date.

"I'm really sorry, Serena, but I have to go. I think my little sister is in trouble. You can stay and watch the concert if you want to," Dan said, his dad's band was about to go on and he was having an amazing time with Serena, but he had to go help Jenny.

"Why don't I come with you?" Serena suggested, "I might as well see what I'm missing, plus I may be able to help you find Jenny.

"Yeah, okay," Dan agreed as they hopped in the cab and headed out into a huge traffic jam.

Back at the Kiss on the Lips party, Nate was going crazy looking for Jenny. He had looked everywhere for her, even peeking into the bathrooms, but there was still no sign of her. Then he noticed a staircase that led to the roof. _Maybe she's up there, _he thought and ran up the stairs too quickly to see Chuck Bass's scarf lying on the second landing

**Spotted: C and N fighting on the roof at the Kiss on the Lips Party. Careful N, you don't want B finding out that you're defending some other girl's honor.**

"Chuck," Nate shouted when he reached the roof and saw his friend with a girl, "I'm looking—" Nate stopped mid-sentence, his eyes wide with horror as he realized what was happening. The girl who had been pinned under Chuck came running towards him finally freed, tears streaming down her face, disheveled, and shaking.

"Jenny? Jenny, what happened? Are you okay?" Nate asked, while wrapping her up in his suit jacket and guiding her inside the stairwell to calm down and wait, while he handled Chuck._ How could Chuck do this to Jenny? _ _How could Chuck do this to anyone? _He thought as he ran towards Chuck and grabbed him by the shirt collar pinning him down against the skylight, where Jenny had been moments earlier.

"What the fuck is your problem Nathaniel, you jealous or something?' Chuck spat at Nate.

"You fucking son of a bitch, you had no right to touch her," Nate spat back at Chuck angrily.

"Why the hell do you care what I was doing with her? She's not your girlfriend. She's not your sister. Hell, she's barely even your friend. So why do you care?" Chuck said with acid in his voice.

"I CARE BECAUSE SHE'S A PERSON, NOT A THING!! YOU CAN'T DO THAT TO HER CHUCK!!" Nate screamed as he slammed his fist into Chuck's face, "WE'RE DONE, YOU HEAR ME? DONE. YOU BETTER STAY THE FUCK AWAY FROM ME _AND_ JENNY! IF I EVER CATCH YOU EVEN LOOKING AT HER AGAIN I'LL FUCKING KILL YOU!" Nate let Chuck up and started walking away.

"Nate, please, you're my best friend, you don't understand. You can't just—" Nate didn't even let Chuck finish.

"I said we're done, Chuck," Nate said coldly, walking back to the door that Jenny still stood behind.

"Your life is over, Nate, hers is too. Don't forget I know everything," Chuck shouted after Nate.

"Let's go," Nate said to Jenny in a kind brotherly tone, placing his hand on the small of her back to guide her down the stairs.

**Spotted: Little J and N making a very public exit from B's party. Too bad for them there's school on Monday and people talk. **

Blair Waldorf was standing in the middle of the room looking for Nate when she saw them. Nate guiding Jenny down the stairs, his jacket on her shoulders, his hand on her back. "Nate!" Blair yelled to him, but he didn't seem to hear her, he was too busy playing big brother or maybe something worse to Jenny Humphrey.

"Are you sure you're okay?" Nate asked Jenny in a whisper, lacing his fingers with hers, so he wouldn't lose her in the crowd.

"Yeah, I will be. I just want to go home. Can you help me get a cab?" Jenny said meekly.

"I'm not really comfortable leaving you alone after what just happened to you up there, Jenny. Why don't you let me take you home?" Nate said in a protective, big brother-like tone that only Dan himself could rival.

"Okay," Jenny agreed without a second thought. She felt completely at ease with him after what he had just done for her.

Nate guided her though the crowd to the door, not caring for a second who saw, and put her in the limo, getting in after her.

"That stupid freshman better not show her face around here again," said Chuck Bass, who was standing behind Blair at the door, holding a towel on his nose, as the limo sped away.

"Actually, I'm kind of hoping she does," said Blair, because if there was one thing she knew, it was to keep her friends close, and her enemies closer.

Nate sat close to Jenny, stroking her hair in the way he imagined her brother Dan would, as she rested her head on his shoulder and closed her eyes. Nate knew there would be major consequences for what he had just done, but he didn't care. He was determined to take care of Jenny Humphrey. He was determined to protect her.


	8. Chapter 7: The AftermathIt's a Disaster

Chapter Seven: The Aftermath/It's a disaster

**Spotted: N spending time in Brooklyn. He better just hope people don't get the wrong idea.**

"Thanks so much for driving me home Nate, you really didn't have to do that. Hopefully Blair won't be too mad at you, or worse, at me," Jenny said as she and Nate walked towards the door of her loft in Brooklyn.

"Jenny, it really wasn't a problem, I'm just glad I was able to help you. It honestly makes me sick that Chuck was trying to take advantage of you that. As for Blair, don't you dare worry about that, I'll explain what happened to her and all will be forgiven, Nate said still stroking Jimmy's hair in a calming big brotherly way as she opened the door.

Jenny cringed at Nate's mention of Chuck and at the idea that people would know what happened to her at the party. She felt so stupid for thinking that Chuck Bass just wanted to talk to her. "Thanks again, Nate, I don't know what I would've done today without you," Jenny smiled.

"Hey Jenny," Nate called as she was about to walk inside, "I think I better wait around here with you for a while, you know just to make sure you're okay, at least until Dan gets home."

_I really hate when people treat me like I'm five years old, but I guess after my stupid behavior tonight, I kind of deserve it. And he's just trying to look out for me. And he is kind of cute, okay, really cute. And I'm already in trouble with Blair; I'm sure, so why not spend a few more minutes with Nate while I'm still allowed. He must think I'm so stupid. Oh shit, I better call Dan and tell him that I'm okay, _Jenny thought before giving Nate an answer. "Well, despite what you might think, I really am okay, but if it would make you feel better you can come in for a little bit," Jenny said as Nate followed her inside. She sat down on the couch and pulled out her phone to call her brother.

"Jenny? Jenny, what's the matter? Are you still at the party? Are you okay? I'm sorry it's taking me so long were just caught in the traffic," the words rushed out of Dan's mouth so fast that Jenny could barely say a word.

"Dan! Dan, calm down! I'm fine. A friend of mine helped me out and took me home, he insisted on waiting with me until you got home. I just wanted to call and say not to worry about me," Jenny answered her brother in the most nonchalant way possible.

"Jen, you didn't answer my question. What happened to you?" Dan desperately wanted an answer, Jenny was his little sister, so it was only natural for him to worry about her.

"Dan, I'm tired, please don't worry, I'm fine now and that's all that matters, Jenny answered not wanting to rehash the events of earlier that evening. "Nate?" She asked when she hung up the phone, "isn't Blair going to be looking for you? Don't you have to get home?

"Jenny don't worry about me, I can handle everybody in my world. I know who to trust and who avoid and I know how to deal with everyone, maybe I can help you in figuring that out. Are you sure you're okay?" Nate said.

"Nate! I swear I'm fine! I was just stupid, that's all. Right now I'm tired," Jenny said, annoyed by how much Nate was reminding her of Dan at that moment.

"Jenny," Nate said sweetly, "I really didn't mean to upset you, I'm sorry. And you are not stupid, you just trust people too much. If you're tired, why don't you go lay down, I will wait until your brother gets home and explain things to him.

"Nate, thanks for rescuing me. I promise you I am fine. I'm just feeling like a complete idiot for letting that happen to myself," Jenny said as she walked to her room to change out of her dress and into sweatpants.

"Jenny," Nate called after her, "it's not your fault, and you can't blame yourself. Chuck did this to you, not the other way around."

"Yeah I know, and I'm fine, just stop asking me about it okay?" Jenny said because she was starting to feel like she was going to have two big brothers. She came back and sat next to Nate on the couch. She liked the way he made her feel, so safe, so comfortable, so warm. She felt she could trust him completely. Jenny closed her eyes and started to fall asleep; Nate started stroking her hair again. She felt like she could stay this way forever. She felt like Nate would never let anything bad happen to her. A few minutes later, Jenny was asleep on the couch and Nate was watching over her, one hand still stroking her hair in a brotherly fashion, when Dan opened the door and entered the loft with Serena in tow.

"Hey, thanks for stepping in man," Dan said quietly to Nate noticing his little sister asleep on their couch. What the fuck happened to her anyway?"

"Chuck Bass," Nate said barely able to contain his disgust and anger.

"What? What do you mean Chuck Bass happened?" Dan asked now sitting down and stroking Jenny's hair the way Nate had been before.

"Dan," Serena said before Nate could answer, "I think when he was trying to tell you, is that the most despicable person, and most notorious womanizer on the Upper East Side, not to mention his best friend, tried to take advantage of your little sister."

"That fucking bastard. How could he. She's 14 years old. What gave him the right? I'm such a bad brother, I can't believe I didn't get there in time, I'll kill him" Dan was so angry he could barely think straight. "Hey wait a minute," he said to Nate, "Who the hell are you and how do you know Jenny was in trouble?" Dan said, his protective older brother instincts running on overdrive.

"I'm Nate Archibald, and I know your sister. She sent me a text message telling me she was in trouble and I knew she was at the party, so I went looking for her and found my former best friend causing her "d a lot of trouble," Nate said leaving out important details like, _"I have a huge crush on your little sister and I'm also hopelessly in love with the girl that you just took out on a date."_

"Alright," Dan said, feeling slightly suspicious of Nate's motives, but more than anything feeling grateful that Nate had been there to take care of Jenny. "Hey Serena, I'm really sorry, but I have to stay here with Jenny, but I had an awesome time with you tonight."

"Dan," Nate said, feeling himself inexplicably pulled towards the little freshmen girl sleeping on the couch, "I can say here with Jenny, while you take Serena home, it's no problem."

Serena smiled at Nate, feeling grateful for his offer. She was having a lot of fun with Dan and wasn't quite ready for their date to be over.

Dan thought about it for a minute._ I really like this girl, and I want to spend more time with her. But I'm not sure if I should really trust Nate, I mean he did rescue Jenny from Chuck and everything, but I can't help thinking that he has some ulterior motives. I should really be here to make sure she is okay, but it won't take long. What should I do? Jenny would probably tell me to take Serena home. It was a very gentlemanly thing of Nate to do, offering to stay with Jenny like that. He really wanted to take Serena home so maybe he should._ "Well, if you're sure it's not a problem for you, that would be great," Dan finally answered.

"Okay, then. See you later Serena, Dan," Nate said, a bittersweet feeling washing over him. He hated to watch Serena with Dan, but he loved being with Jenny. He felt so protective of her, it was almost painful.

**Spotted: S and Lonely Boy headed for the Upper East Side. Could this be more than just a fling?**

"I'm really glad you stuck with me through all of this tonight; I had a great time with you, in spite of everything," Dan told Serena sincerely.

"I had a great time with you too. You're a really great guy, Dan," Serena smiled back at him. _I can already tell you're different than most of the people I know—in a good way though. I barely know you, but somehow, for some reason, I feel like I can trust you, like you won't judge me. I feel like you'll accept me for who I really am. I can already tell that I don't have to pretend with you; I feel like I can really be myself with you. No games. No lies. I just hope you didn't pick up on anything between me and Nate, because I don't want Nate anymore. He's Bair's boyfriend and he's falling hard for Jenny, real hard, I can tell. He will figure out that he doesn't want me anymore soon enough, I know that. Anyway, I want __**you**__, I really do, _Serena thought to herself and wanted to add.

"Thanks," Dan replied, "and speaking of great guys, what's Nate's deal anyway?" Dan asked.

"His deal?" Serena asked confused.

"Yeah, his deal, does he enjoy playing the knight in shinning armor or something like that? Should I have trusted him to be alone with Jenny?" Dan asked Serena, hiding his growing panic.

"Don't worry about Nate, Dan. He is a really good guy and he was just looking out for Jenny. Trust me, you have nothing to worry about,, Serena said with a smile, but kept the truth hidden. What she was thinking was:_ Nate's not a bad guy unless you consider cheating on your girlfriend with her best friend a bad thing. Nate is looking out for Jenny but his intentions are entirely pure. He obviously likes her and I can't believe you are too blind to see that,_ but Serena kept these thoughts to herself. She Nate well enough to know he was no threat to Jenny and she didn't want Dan to worry about Jenny right now.

**Spotted: N choosing Little J over Queen B. again. Looks like there might be trouble brewing in Paradise.**

Nate could feel his cell phone vibrating in his pocket, but he didn't really want to answer it. He was pretty sure it would be Blair demanding to know why he had run out of the party with Jenny Humphrey. He was pretty sure she would be angry, but he knew that she wouldn't do the dirty work for him. Nate Archibald was beginning to realize that no matter how angry he made Blair Waldorf, no matter how much they both knew that this relationship wasn't working she wouldn't break up with him. He wanted to just end it right then and there, but he knew that was impossible. Somehow some way he would be forced to get back together with Blair even though she was not the person he wanted to be with. Although, he would admit to himself that he wasn't sure he wanted to be with at that moment. So he reluctantly picked up his cell phone and looked at the screen.

**Blair (mobile)**

**WHERE RU?? HOW COULD U JUST LEAVE??? **

**Y DID U HIT CHUCK??? U BETTER B BRUNCH 2MORROW!!!**

Nate slammed his phone shut seething with anger._ Who the fuck does Blair think she is? She may be my girlfriend right now, but she has no right to control my life! Why the fuck does she give a shit about what I did to Chuck anyway? I really don't want to go to that fucking brunch but I have no choice. If I don't keep Blair happy my father will kill me because for some reason he thinks that the success of his business deal with Eleanor Waldorf is dependent on the success of my relationship with Blair. I may have to go, but that doesn't mean I have to do exactly what they want me to do,_ Nate thought as he looked at Jenny who was asleep on the couch next to him. He pitied her in a strange sort of way because he knew how much she wanted to be like Blair and wanted to be Queen of Constance and the Upper East Side, but he also knew that she was innocent and naïve and she didn't realize what she would have to sacrifice, or who she would have to hurt to get to the top and stay there. Nate closed his eyes and felt peace wash over him because he knew that for now at least, he didn't have to be part of that world and neither did Jenny.

**Spotted: Lonely Boy walking S. to her door. Who knew gentlemen came from Brooklyn?**

"You were a pretty good day for someone I don't know," Serena laughed as she stepped out of the cab, hoping he would walk her to her door.

"You too. Let me walk you to your door," Dan answered with a smile as she grabbed her hand. "We should definitely go out again sometime," he said with confidence he never felt before.

"Yeah, maybe we should," Serena said trying to hide her excitement. Dan was different than any other guy she knew and she liked being around him.

The reached her door and there was an awkward pause. Serena was pretty sure that Dan wanted to kiss her and she knew that she wanted to kiss him too.

**Spotted: Queen B. alone without any reinforcements. Could her kingdom the crumbling before her eyes or is there a surprising knight in shining armor waiting for her?**

Blair couldn't believe how wrong tonight had gone for her. First, her boyfriend had gotten in a fight with his best friend over another girl, a freshman no less. Then he ditched her at her big party to run off with the girl he had been fighting over, who was Jenny Humphrey from Brooklyn! He'd picked a stupid freshman wannabe who wasn't even from the Upper East Side over her. This was unbelievable! Then Nate had ignored her text messages. She couldn't help feeling like he had ulterior motives for helping Jenny, and that made her think of Nate's confession earlier that day, he had slept with her best friend, Serena Van der Woodsen while they were dating. Blair knew that she should break up with Nate, but for some reason she just couldn't. Maybe it was because she felt like they were meant to be together. Maybe it was because she was afraid of what other people would think and of how it would affect the power structure at Constance, especially now that her ex-best friend and former Constance it girl Serena was back in the picture. Most likely, it was because Blair Waldorf saw her life like a movie and she liked happy endings and hated to fail, breaking up with Nate Archibald, her first and only boyfriend, would be admitting failure and destroying her happy movie like ending all at once, and Blair just couldn't handle that.

"Miss Blair, you have visitor," Derota said in her heavily accented voice.

"Who is it?" Blair asked trying to disguise her tear choked voice with a tone of annoyance.

"Mr. Chuck," Derota replied.

_Chuck? What did Chuck from her at a time like this? Nate had just kicked his ass at the same time he broke Blair's heart, so maybe Chuck wanted to commiserate._ "Send him up," Blair called down from her room.

Seconds later, Chuck Bass was standing in her doorway smirking.

"He doesn't care about you, and he never will. He doesn't realize how lucky he is to have you. I say you get even with him, and the stupid sluts who stole his heart and ruin your life. I'll help you," Chuck said skipping all of the pleasantries.

"Why do you care, Chuck? What's in it for you? Why would you help me?" Blair asked bitterly turned her face away from him.

"He destroyed my face and my reputation. He spit on our friendship for a stupid freshman girl. I'm Chuck Bass, nobody, not even Nate Archibald gets away with treating me like that," Chuck responded fluidly hiding his true intentions. The real reasons he had come here floated around in his head, "_she doesn't appreciate you. You are so amazing and so beautiful, those other girls look like trash next to you. I want you. I love you."_

"Well fine," Blair answered, "since you here with this proposal you must have a plan."

"As a matter of fact I do," Chuck answered with a smirk.

**Spotted: Lonely Boy and S. kissing in the rain. Looks like lonely boy made an impression.**

The tension was rising in front of Serena's building and all Dan wanted to do was kiss Serena. As if the sky felt the romantic tensions between them, the clouds opened up and it began to rain. Suddenly, Dan felt bold. Before he could even realize what he was doing, Dan Humphrey kissed Serena, the girl he had a crush on since he first saw her. A few seconds later, he wanted to pull back feeling certain that he shouldn't have done it, but Serena wouldn't let him go. So they stood there together kissing in the rain and everything else seemed to disappear around them, it was perfect. When they finally separated, Serena smiled and said, "So about that second date, would you like to come to brunch with me at the Palace tomorrow. My mom is making me go and I really don't want to, but I think I would feel a lot better if you came with me.

"Sure, that sounds great!" Dan responded, still in a euphoric state.

Serena smiled back at him as she opened her door and went inside.

**Spotted: D. (formerly known as lonely boy) checking up on Little J., but is he the only one?**

"Dan, I'm fine! I swear! I've been fine every time that you've asked me! I was fine last night when Nate left, and when I went to bed, and I'm fine now! I promise!" Jenny told her brother, not bothering to hide the exasperation in her voice.

"Jen, I know and I'm sorry, but I can't help worrying about you. I'm your big brother, that's my job, it's what I do. And if you ever decide you're not okay and you want to talk to somebody who's not, well you know, me or Nate, just let me know," Dan said, stunned that he mentioned Nate, even in passing, but he had to admit Nate had done a lot better job of taking care of Jenny last night then he had.

"Yeah, okay Dan, I will, I promise," Jenny said with a meek smile. "Now onto more important things," she said immediately brightening up, "how was your date with Serena last night?"

"It was good. I'm actually getting ready to go meet her for some brunch thing pretty soon," Dan told his little sister.

"Brunch at the Palace?" Jenny asked in awe, then quickly added, "I hope you're not planning on wearing THAT!"

Dan smiled at his sister and ruffled her hair before walking out of the room.

Jenny had to do some damage control, and she knew exactly where her first stop was, Blair Waldorf's apartment.

**Spotted: Little J. on the Upper East Side headed for B's building. Hopefully B plays nice, who am I kidding I love a good fight!**

"Derota, I told you no visitors—Oh Jenny, what you want," Blair greeted her guest with a sly smile only second to Chuck Bass's.

"I just realized I still had your calligraphy pens and I wanted to return them," Jenny said, hopelessly trying to hide the true reasons for her visit.

"That is the lamest excuse I've ever heard," Blair said coldly, "you want to know what people are saying about you."

"Are they saying anything? You know about what happened?" Jenny asked, her voice full of embarrassment.

"No, not really, at least not yet anyway. Chuck usually likes to brag about his conquests not his victims. Although, a few people are talking about the way my boyfriend whisked you away last night," Blair said as she twirled a strand of hair around her finger.

"I'm so sorry about that Blair! I didn't know he was going to do that! It was just that I was in trouble and I didn't know who to call other than my brother who was on a date with Serena and when I met Nate he said if I ever need help I should call him and so I did but I didn't expect him to take me home or anything but he insisted and so I'm really really really sorry I ruined your party and I hope you forgive me!" The words came out of Jenny Humphrey's mouth so fast that she was barely coherent.

"Calm down Jenny, I know it wasn't your fault. Nate is just like that, he likes to take care of everyone. I'm just a little sad you didn't come to me for help. After all, we are friends, right?" Blair said, her voice full of fake sweetness.

"I'm just glad that nobody is really talking about it and that your not too angry at me about what happened with Nate," Jenny said with a smile, thinking that this whole ordeal had been a lot less painful than she had envisioned.

"Like I said Jenny, why would I be mad at you? It's your fault that Nate feels the need to rescue every stupid girl gets herself into trouble. As far as people talking about what happened is concerned, you have to remember that if you want to be in this world, people will talk about you eventually, and you need to decide if all this is worth it," Blair said gesturing around the room. She had expertly convinced Jenny Humphrey that there were no hard feelings about what had transpired last night, but her thoughts told a different story._ "Yeah sure, we're good, As long as you keep your low class hands off my boyfriend. You're not cut out for this world, this life. You too naïve and trusting. But I can use you for now and you really are no threat to me._ "Jenny," Blair added as an afterthought, "help me get ready for brunch."

"Okay," Jenny agreed enthusiastically, happy to be back in Blair Waldorf's good graces. Blair led Jenny up the large spiral staircase to her bedroom, and Jenny looked around in awe. Everything was so beautiful, so perfect. This room was most definitely fit for a queen, and Blair filled the role perfectly.

"It's beautiful," Jenny said, pointing to a blue strapless dress that was playing on Blair's bed.

"It's average," Blair responded, "the color is so last season, and besides Stella McCartney has a much nicer version at Bendels. If you like it so much you can have it,"

"Really? No, I couldn't," Jenny was ecstatic, but something about the offer didn't feel right to her.

"Really, it's fine. I have a closet full of dresses like that. I don't even like that one very much anymore," Blair said, insisting that Jenny take the dress. She took it, it would mark her as one of Blair's crowd, and make it that much harder for Jenny to betray her.

"Well okay, I guess you really don't want it. Thanks for everything, Blair," Jenny said as she turned to leave.

"Anytime Jenny," Blair said with a smile, "remember we are friends. Friends help each other and don't betray each other," Blair added a subtle warning.

**Spotted: N headed to Brooklyn for the second time in less than 24 hours. Whoa, he must really have it bad for Little J.**

"Nate!" Jenny exclaimed in surprise when she answered her door, "what are you doing here? Doesn't brunch start soon? Aren't you supposed to be there? With Blair? Won't she be angry if you don't show up?"

"Jenny, relax. I was in the neighborhood and I just came by to make sure you're doing okay," Nate answered easily.

"Oh no," Jenny groaned, "I swear, it's like you and Dan were separated at birth or something! I'm fine! I appreciate all the help and concern, and you seem like a really nice guy, but you can't be here! You're going to get me in trouble with Blair, Nate, and I really don't need that right now,"

"Jenny, I'm your friend and I want to look out for you. You may think of Blair as some kind of Constance royalty, but that doesn't mean she can control your life. She's my girlfriend, and she certainly does not control mine. There is no reason we can't be friends," Nate said trying to hide his exasperation, he really hated how everyone let Blair control their lives.

"Okay fine," Jenny said with a big smile, "you win, we're friends and there's nothing Blair can do about it.

"Good," Nate said flashing Jenny one of his knee-weakening, perfect smiles. "Now I have a confession to make, there is another reason I came here this morning. I think that after the night you had, you should not be hanging out here alone, moping around, and not even changing your clothes from last night."

At the last statement, Jenny blushed scarlet red. She hadn't even realized she was still in the clothes she changed into last night after Nate brought her home from the party. She was even more embarrassed when she realized that she'd worn those clothes over to Blair's house. "Well then what do you propose I do instead? I just humiliated myself in front of everyone who matters at our school and thankfully I narrowly escaped social execution by your girlfriend," Jenny shot back a little annoyed at Nate.

"Well, I propose that you come to brunch with me today. It'll keep me from being bored to tears, and I think you'll have fun," he answered without a second thought.

"Nate, you know I can't! It's Chuck's dad's hotel and Blair will be really angry if you bring me. You know that Nate," Jenny said, frustrated and a little confused as to why he wanted her to go so badly. She assumed he was just being protective, but things didn't seem to add up.

"First of all, don't you dare worry about that asshole Chuck, if he causes any problems I'll take care of it. Second of all, you need to have some fun and I'm not going anywhere unless you come with me, so if you think Blair will be angry that I bring you, just think how angry she'll be I don't show up at all," Nate said with a devilish smile.

"Nate, just go. I'm not coming and you can't make me," Jenny said hoping he was bluffing about not going to brunch without her.

"I'm not going anywhere, like I said, you're coming with me you need to get out of this house," Nate was insistent.

"Ugh, fine you win! If it will get you to go, I'll come. Just give me some time to get ready," Jenny said as she grabbed the blue dress that Blair gave her off the couch. "But don't say I didn't warn you that this wasn't a good idea," she added as she looked back at him.

**What do you get when you combine D, S., B., N, C., Little J. and a high-class Sunday brunch at the Palace Hotel? Fireworks, that's what and I can't wait! **

A little over 20 minutes later, Jenny was stepping out of Nate Archibald's limo in front of the Palace Hotel, wearing the blue strapless dress Blair had given to her. As shocked as she was to be there, she had to admit she was a little excited.

"This will be fun, I promise," Nate reassured her as they headed inside, although he knew there would probably be drama he was sick of playing by everybody else's rules. Jenny was just his friend, he convinced himself, and there was nothing wrong with him bringing her here.

When they walked inside, Blair, who was standing near Chuck smiled at Nate, happy that he put aside all of his crazy behavior from last night and showed up, but her happiness quickly turned to displeasure when she saw Jenny Humphrey following him through the door.

"What is she doing here?" Blair hissed in Chuck's ear.

"How am I supposed to know? Looks like your loser boyfriend invited the whore. I told you he doesn't care about you," Chuck hissed back.

"Of course he cares about me, he's just concerned about her because of what _you_ tried to do last night," Blair said trying to convince herself as much as Chuck that Nate still cared about her.

"Whatever you need to tell yourself. I can't believe that Nate and Serena think it's okay to bring Brooklyn trash to brunch," Chuck said.

"What are you talking about? I mean I know Jenny's here, but that doesn't mean Nate brought her, and what does Serena have to do with that?" Blair asked.

"Look over there," Chuck said pointing to Serena who was arm in arm with Dan Humphrey.

"Who does she think she is? Showing up here like that," Blair said and started over to where Serena, Dan, Jenny, and Nate were standing.

Meanwhile, on the other side of the room, Dan was shocked to see his little sister at an Upper East Side brunch, especially with Nate Archibald.

"Jenny, what are you doing here? Dan asked not even bothering to hide his surprise.

"I told Nate he should bring her so that she wouldn't think all Upper East Side events were as crazy as that party last night. I didn't want your sister's high school experience to be defined by one awful party," Serena jumped in without a second thought. She really didn't know why Nate had brought Jenny here, but didn't want the situation to get anymore awkward. Serena shot Nate a meaningful look, imploring him for an explanation of his bizarre behavior when it came to Jenny Humphrey. The only other girl she'd ever seen Nate act so crazily for was her and she didn't like where this was going. She knew he still thought he liked her and she could see that he was falling for Jenny, but she could also see that this was trouble.

"Yeah, Nate told me that Serena thought I would enjoy brunch, and then she sent him to come get me," Jenny said picking up on the glances and deciding to play along.

"Oh Serena, it was nice of you to worry about Jenny that way, but did you warn her not to repeat your mistakes when it comes to guys like Nate," said Blair Waldorf in a cold and bitter voice from behind.

"What is she talking about?" Dan and Jenny asked practically in unison.

"Oh how cute! Neither of them knows about your little… transgressions," Chuck said coming from behind Blair.

"Serena, what are they talking about?" Dan asked.

"Well Serena, do you want to tell him or should I?" Blair asked in a cold emotionless voice.

"There's nothing to tell, what happened is in the past and I'm not like that anymore, you should know that Blair," Serena said angrily.

"Oh come on S., he deserves to know that you're as much of a whore as his little sister," Chuck said before Blair had a chance to respond.

"MY SISTER IS NOT A WHORE!!! Serena, what are they talking about? What happened?" Dan said struggling to contain his rage.

"She slept with Nate while we were dating, but it looks like Nate is trying to convince your sister to repeat Serena's mistake, I think she's smarter than that though," Blair said bluntly.

"I really liked you, I thought you were different, but now I see you're no better than the rest of them," Dan told Serena angrily, "and you I thought you were a good guy, I guess I was wrong," Dan said to Nate. "Come on Jenny, let's go home. This world is just too crazy!" Dan said, grabbing Jenny's hand, and storming out of the Palace. Serena and Nate ran after them.

"Dan," Serena yelled, "you have to believe me, I'm not like that anymore, and I really like you, Blair is just a vindictive bitch she wants to run everyone else's life because she's not happy, Dan please, don't walk away from me!" The tears were streaming down Serena's face.

"Jenny, Dan, you know how Blair can be, it was like that with you, Jenny. I just wanted to be your friend, nothing else, I promise!" Nate said in a pleading tone.

Dan did nothing, he just kept on walking. Jenny looked back sadly, she'd been right about one thing it was a disaster.

**A/N: I'm sorry it took me so long to update!! I was busy moving in and getting adjusted to college! Hopefully this long chapter makes up for it! I promise to update more frequently. Up next is the masquerade ball, Blair's birthday and a unique chance for Nate and Chuck to make up. Please stick with me I'm really excited for where this story is going next!**


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